JP2003104878A - 皮脂生産を阻害するためのワックス・エステルとコレステリル・エステル合成の２重阻害剤 - Google Patents
皮脂生産を阻害するためのワックス・エステルとコレステリル・エステル合成の２重阻害剤Info
- Publication number
- JP2003104878A JP2003104878A JP2002222616A JP2002222616A JP2003104878A JP 2003104878 A JP2003104878 A JP 2003104878A JP 2002222616 A JP2002222616 A JP 2002222616A JP 2002222616 A JP2002222616 A JP 2002222616A JP 2003104878 A JP2003104878 A JP 2003104878A
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- bis
- methylethyl
- carbon atoms
- alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- -1 cholesteryl ester Chemical class 0.000 title claims abstract description 316
- 210000002374 sebum Anatomy 0.000 title claims abstract description 47
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 31
- 230000002401 inhibitory effect Effects 0.000 title claims abstract description 26
- 230000015572 biosynthetic process Effects 0.000 title abstract description 13
- 238000003786 synthesis reaction Methods 0.000 title abstract description 9
- 239000004164 Wax ester Substances 0.000 title abstract description 8
- 235000019386 wax ester Nutrition 0.000 title abstract description 8
- 229940125436 dual inhibitor Drugs 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 251
- 150000003839 salts Chemical class 0.000 claims abstract description 67
- 239000012453 solvate Substances 0.000 claims abstract description 49
- PTQXTEKSNBVPQJ-UHFFFAOYSA-N Avasimibe Chemical compound CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1CC(=O)NS(=O)(=O)OC1=C(C(C)C)C=CC=C1C(C)C PTQXTEKSNBVPQJ-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000005516 coenzyme A Substances 0.000 claims abstract description 9
- 229940093530 coenzyme a Drugs 0.000 claims abstract description 9
- 108700016155 Acyl transferases Proteins 0.000 claims abstract description 6
- 102000057234 Acyl transferases Human genes 0.000 claims abstract description 6
- 150000002191 fatty alcohols Chemical class 0.000 claims abstract description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 192
- 125000000217 alkyl group Chemical group 0.000 claims description 167
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 160
- 229910052739 hydrogen Inorganic materials 0.000 claims description 83
- 239000001257 hydrogen Substances 0.000 claims description 82
- 206010000496 acne Diseases 0.000 claims description 67
- 208000002874 Acne Vulgaris Diseases 0.000 claims description 63
- 150000002431 hydrogen Chemical group 0.000 claims description 40
- 125000001424 substituent group Chemical group 0.000 claims description 40
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 38
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 36
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 36
- 229910052794 bromium Inorganic materials 0.000 claims description 36
- 239000000126 substance Substances 0.000 claims description 34
- 125000003545 alkoxy group Chemical group 0.000 claims description 33
- 239000000460 chlorine Substances 0.000 claims description 33
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 32
- 229910052801 chlorine Inorganic materials 0.000 claims description 32
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 32
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 30
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 30
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 26
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 26
- 229910052760 oxygen Inorganic materials 0.000 claims description 26
- 239000001301 oxygen Substances 0.000 claims description 26
- 241000282414 Homo sapiens Species 0.000 claims description 25
- 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 claims description 25
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 19
- 125000002950 monocyclic group Chemical group 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- 229920006395 saturated elastomer Polymers 0.000 claims description 19
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 18
- SWYZGLWCQFMQJW-UHFFFAOYSA-N phenoxy hypofluorite Chemical compound FOOC1=CC=CC=C1 SWYZGLWCQFMQJW-UHFFFAOYSA-N 0.000 claims description 18
- 239000000243 solution Substances 0.000 claims description 18
- 150000002430 hydrocarbons Chemical class 0.000 claims description 17
- 239000008194 pharmaceutical composition Substances 0.000 claims description 17
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 17
- 108090000790 Enzymes Proteins 0.000 claims description 16
- 102000004190 Enzymes Human genes 0.000 claims description 16
- 150000002148 esters Chemical class 0.000 claims description 16
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 claims description 14
- 206010039792 Seborrhoea Diseases 0.000 claims description 13
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 13
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- 239000011593 sulfur Substances 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 11
- 125000000623 heterocyclic group Chemical group 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 239000007983 Tris buffer Substances 0.000 claims description 9
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 8
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- 125000004429 atom Chemical group 0.000 claims description 8
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 8
- 230000000694 effects Effects 0.000 claims description 8
- 125000004434 sulfur atom Chemical group 0.000 claims description 8
- 230000000699 topical effect Effects 0.000 claims description 8
- 230000003902 lesion Effects 0.000 claims description 7
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 239000011737 fluorine Chemical group 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 230000037312 oily skin Effects 0.000 claims description 6
- 239000004215 Carbon black (E152) Substances 0.000 claims description 5
- LXLYXCFZXXKURC-UHFFFAOYSA-N [2-[2,4,6-tri(propan-2-yl)phenyl]acetyl]sulfamic acid Chemical compound CC(C)C1=CC(C(C)C)=C(CC(=O)NS(O)(=O)=O)C(C(C)C)=C1 LXLYXCFZXXKURC-UHFFFAOYSA-N 0.000 claims description 5
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 5
- 229930195733 hydrocarbon Natural products 0.000 claims description 5
- 201000004624 Dermatitis Diseases 0.000 claims description 4
- HCNHIFFZTIRZJA-UHFFFAOYSA-N [3-[2-(2,6-dichlorophenyl)acetyl]-2,6-di(propan-2-yl)phenyl] sulfamate Chemical compound CC(C)C1=C(OS(N)(=O)=O)C(C(C)C)=CC=C1C(=O)CC1=C(Cl)C=CC=C1Cl HCNHIFFZTIRZJA-UHFFFAOYSA-N 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 4
- 208000008742 seborrheic dermatitis Diseases 0.000 claims description 4
- KFDFYCRDUBAKHD-UHFFFAOYSA-M sodium;carbamate Chemical compound [Na+].NC([O-])=O KFDFYCRDUBAKHD-UHFFFAOYSA-M 0.000 claims description 4
- 125000000579 2,2-diphenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(C1=C([H])C([H])=C([H])C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 208000009675 Perioral Dermatitis Diseases 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 239000003246 corticosteroid Substances 0.000 claims description 3
- AQYSYJUIMQTRMV-UHFFFAOYSA-N hypofluorous acid Chemical compound FO AQYSYJUIMQTRMV-UHFFFAOYSA-N 0.000 claims description 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 3
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 claims description 3
- MHCQGCLTFBMETG-UHFFFAOYSA-M (1E)-1-[2,6-di(propan-2-yl)phenoxy]-N-[2,6-di(propan-2-yl)phenoxy]sulfonylmethanimidate Chemical compound CC(C)c1cccc(C(C)C)c1OC([O-])=NS(=O)(=O)Oc1c(cccc1C(C)C)C(C)C MHCQGCLTFBMETG-UHFFFAOYSA-M 0.000 claims description 2
- TVUVBASDYPOVBJ-UHFFFAOYSA-N (4-methylpiperazin-1-yl)sulfonylcarbamic acid;hydrochloride Chemical compound Cl.CN1CCN(S(=O)(=O)NC(O)=O)CC1 TVUVBASDYPOVBJ-UHFFFAOYSA-N 0.000 claims description 2
- HZILKBOATJZGNW-UHFFFAOYSA-N 1-(dicyclohexylsulfamoyl)-3-[2,6-di(propan-2-yl)phenyl]urea Chemical compound CC(C)C1=CC=CC(C(C)C)=C1NC(=O)NS(=O)(=O)N(C1CCCCC1)C1CCCCC1 HZILKBOATJZGNW-UHFFFAOYSA-N 0.000 claims description 2
- LZVGQASTEBPKJE-UHFFFAOYSA-N 1-(didecylsulfamoyl)-3-[2,6-di(propan-2-yl)phenyl]urea Chemical compound CCCCCCCCCCN(CCCCCCCCCC)S(=O)(=O)NC(=O)NC1=C(C(C)C)C=CC=C1C(C)C LZVGQASTEBPKJE-UHFFFAOYSA-N 0.000 claims description 2
- RISJQXIPSGBIDZ-UHFFFAOYSA-N 1-(didodecylsulfamoyl)-3-[2,6-di(propan-2-yl)phenyl]urea Chemical compound CCCCCCCCCCCCN(CCCCCCCCCCCC)S(=O)(=O)NC(=O)NC1=C(C(C)C)C=CC=C1C(C)C RISJQXIPSGBIDZ-UHFFFAOYSA-N 0.000 claims description 2
- 241001553014 Myrsine salicina Species 0.000 claims description 2
- XHSNXNMCXYVKIL-UHFFFAOYSA-N OCl[N+]([O-])=O Chemical group OCl[N+]([O-])=O XHSNXNMCXYVKIL-UHFFFAOYSA-N 0.000 claims description 2
- RPFCHZANSTXMQB-UHFFFAOYSA-N [2,6-di(propan-2-yl)-3-(2,2,2-triphenylacetyl)phenyl] sulfamate Chemical compound CC(C)C1=C(OS(N)(=O)=O)C(C(C)C)=CC=C1C(=O)C(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 RPFCHZANSTXMQB-UHFFFAOYSA-N 0.000 claims description 2
- NVCAXWLFXNFPRF-UHFFFAOYSA-N [2,6-di(propan-2-yl)-3-(2-thiophen-2-ylacetyl)phenyl] sulfamate Chemical compound S1C(=CC=C1)CC(=O)C=1C(=C(C(=CC1)C(C)C)OS(N)(=O)=O)C(C)C NVCAXWLFXNFPRF-UHFFFAOYSA-N 0.000 claims description 2
- BOGOAOVZHJYIRZ-UHFFFAOYSA-N [2,6-di(propan-2-yl)-3-(2-thiophen-3-ylacetyl)phenyl] sulfamate Chemical compound S1C=C(C=C1)CC(=O)C=1C(=C(C(=CC1)C(C)C)OS(N)(=O)=O)C(C)C BOGOAOVZHJYIRZ-UHFFFAOYSA-N 0.000 claims description 2
- RNYUYZOQGFPICG-UHFFFAOYSA-N [2,6-di(propan-2-yl)-3-[2-(2,4,6-trimethoxyphenyl)acetyl]phenyl] sulfamate Chemical compound COC1=CC(OC)=CC(OC)=C1CC(=O)C1=CC=C(C(C)C)C(OS(N)(=O)=O)=C1C(C)C RNYUYZOQGFPICG-UHFFFAOYSA-N 0.000 claims description 2
- LXSBEGRJNHLGJI-UHFFFAOYSA-N [2,6-di(propan-2-yl)-3-[2-(2,4,6-trimethylphenyl)acetyl]phenyl] sulfamate Chemical compound CC(C)C1=C(OS(N)(=O)=O)C(C(C)C)=CC=C1C(=O)CC1=C(C)C=C(C)C=C1C LXSBEGRJNHLGJI-UHFFFAOYSA-N 0.000 claims description 2
- FFHDHZYMGPGQLF-UHFFFAOYSA-N [2,6-di(propan-2-yl)-3-[2-[2,4,6-tri(propan-2-yl)phenoxy]acetyl]phenyl] sulfamate Chemical compound CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1OCC(=O)C1=CC=C(C(C)C)C(OS(N)(=O)=O)=C1C(C)C FFHDHZYMGPGQLF-UHFFFAOYSA-N 0.000 claims description 2
- PZVXVEZHFRHQHE-UHFFFAOYSA-N [2,6-di(propan-2-yl)-3-[2-[2-(trifluoromethyl)phenyl]acetyl]phenyl] sulfamate Chemical compound CC(C)C1=C(OS(N)(=O)=O)C(C(C)C)=CC=C1C(=O)CC1=CC=CC=C1C(F)(F)F PZVXVEZHFRHQHE-UHFFFAOYSA-N 0.000 claims description 2
- WQRMTMWIXSZJNP-UHFFFAOYSA-N [2,6-di(propan-2-yl)-3-[3-[2,4,6-tri(propan-2-yl)phenyl]prop-2-enoyl]phenyl] sulfamate Chemical compound CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1C=CC(=O)C1=CC=C(C(C)C)C(OS(N)(=O)=O)=C1C(C)C WQRMTMWIXSZJNP-UHFFFAOYSA-N 0.000 claims description 2
- KKSWLSQKFBJGQJ-UHFFFAOYSA-N [2,6-di(propan-2-yl)-3-[3-[2,4,6-tri(propan-2-yl)phenyl]propanoyl]phenyl] sulfamate Chemical compound CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1CCC(=O)C1=CC=C(C(C)C)C(OS(N)(=O)=O)=C1C(C)C KKSWLSQKFBJGQJ-UHFFFAOYSA-N 0.000 claims description 2
- MHCQGCLTFBMETG-UHFFFAOYSA-N [2,6-di(propan-2-yl)phenyl] n-[2,6-di(propan-2-yl)phenoxy]sulfonylcarbamate Chemical compound CC(C)C1=CC=CC(C(C)C)=C1OC(=O)NS(=O)(=O)OC1=C(C(C)C)C=CC=C1C(C)C MHCQGCLTFBMETG-UHFFFAOYSA-N 0.000 claims description 2
- HVURYWABVADLBZ-UHFFFAOYSA-N [2,6-di(propan-2-yl)phenyl]sulfamoyl carbamate Chemical compound CC(C)C1=CC=CC(C(C)C)=C1NS(=O)(=O)OC(N)=O HVURYWABVADLBZ-UHFFFAOYSA-N 0.000 claims description 2
- QNRBLGKOBXBNQA-UHFFFAOYSA-N [3-(1-phenylcyclopentanecarbonyl)-2,6-di(propan-2-yl)phenyl] sulfamate Chemical compound CC(C)C1=C(OS(N)(=O)=O)C(C(C)C)=CC=C1C(=O)C1(C=2C=CC=CC=2)CCCC1 QNRBLGKOBXBNQA-UHFFFAOYSA-N 0.000 claims description 2
- OWQGQWCZHWFFBB-UHFFFAOYSA-N [3-(2,2-diphenylpropanoyl)-2,6-di(propan-2-yl)phenyl] sulfamate Chemical compound CC(C)C1=C(OS(N)(=O)=O)C(C(C)C)=CC=C1C(=O)C(C)(C=1C=CC=CC=1)C1=CC=CC=C1 OWQGQWCZHWFFBB-UHFFFAOYSA-N 0.000 claims description 2
- LHGJDLJINRPFDO-UHFFFAOYSA-N [3-(2-cyclohexyl-2-phenylacetyl)-2,6-di(propan-2-yl)phenyl] sulfamate Chemical compound CC(C)C1=C(OS(N)(=O)=O)C(C(C)C)=CC=C1C(=O)C(C=1C=CC=CC=1)C1CCCCC1 LHGJDLJINRPFDO-UHFFFAOYSA-N 0.000 claims description 2
- TVZUKCLORBYVAB-UHFFFAOYSA-N [3-(2-cyclohexylacetyl)-2,6-di(propan-2-yl)phenyl] sulfamate Chemical compound CC(C)C1=C(OS(N)(=O)=O)C(C(C)C)=CC=C1C(=O)CC1CCCCC1 TVZUKCLORBYVAB-UHFFFAOYSA-N 0.000 claims description 2
- LVUYWXXLGSVQEH-UHFFFAOYSA-N [3-(2-phenylacetyl)-2,6-di(propan-2-yl)phenyl] sulfamate Chemical compound CC(C)C1=C(OS(N)(=O)=O)C(C(C)C)=CC=C1C(=O)CC1=CC=CC=C1 LVUYWXXLGSVQEH-UHFFFAOYSA-N 0.000 claims description 2
- WERGUDHVRRAQIA-UHFFFAOYSA-N [3-(2-phenylbutanoyl)-2,6-di(propan-2-yl)phenyl] sulfamate Chemical compound C=1C=CC=CC=1C(CC)C(=O)C1=CC=C(C(C)C)C(OS(N)(=O)=O)=C1C(C)C WERGUDHVRRAQIA-UHFFFAOYSA-N 0.000 claims description 2
- ONKLECGKWMBEJQ-UHFFFAOYSA-N [3-(2-phenylpropanoyl)-2,6-di(propan-2-yl)phenyl] sulfamate Chemical compound CC(C)C1=C(OS(N)(=O)=O)C(C(C)C)=CC=C1C(=O)C(C)C1=CC=CC=C1 ONKLECGKWMBEJQ-UHFFFAOYSA-N 0.000 claims description 2
- WUHZAAZJJIQGBP-UHFFFAOYSA-N [3-(3,3-diphenylpropanoyl)-2,6-di(propan-2-yl)phenyl] sulfamate Chemical compound CC(C)C1=C(OS(N)(=O)=O)C(C(C)C)=CC=C1C(=O)CC(C=1C=CC=CC=1)C1=CC=CC=C1 WUHZAAZJJIQGBP-UHFFFAOYSA-N 0.000 claims description 2
- QLCRUODBCQNCBH-UHFFFAOYSA-N [3-(3-methyl-2-phenylpentanoyl)-2,6-di(propan-2-yl)phenyl] sulfamate Chemical compound C=1C=CC=CC=1C(C(C)CC)C(=O)C1=CC=C(C(C)C)C(OS(N)(=O)=O)=C1C(C)C QLCRUODBCQNCBH-UHFFFAOYSA-N 0.000 claims description 2
- YKPBDXIXQLCDMW-UHFFFAOYSA-N [3-(3-phenylpropanoyl)-2,6-di(propan-2-yl)phenyl] sulfamate Chemical compound CC(C)C1=C(OS(N)(=O)=O)C(C(C)C)=CC=C1C(=O)CCC1=CC=CC=C1 YKPBDXIXQLCDMW-UHFFFAOYSA-N 0.000 claims description 2
- LGCMWWNQMXOKTK-RBUKOAKNSA-N [3-[(1r,2r)-2-phenylcyclopropanecarbonyl]-2,6-di(propan-2-yl)phenyl] sulfamate Chemical compound CC(C)C1=C(OS(N)(=O)=O)C(C(C)C)=CC=C1C(=O)[C@H]1[C@H](C=2C=CC=CC=2)C1 LGCMWWNQMXOKTK-RBUKOAKNSA-N 0.000 claims description 2
- VUKGWEPYJTUIFU-UHFFFAOYSA-N [3-[2-(2,5-dimethoxyphenyl)acetyl]-2,6-di(propan-2-yl)phenyl] sulfamate Chemical compound COC1=CC=C(OC)C(CC(=O)C=2C(=C(OS(N)(=O)=O)C(C(C)C)=CC=2)C(C)C)=C1 VUKGWEPYJTUIFU-UHFFFAOYSA-N 0.000 claims description 2
- VWMCJIVWYXESEB-UHFFFAOYSA-N [3-[2-(2-methoxyphenyl)acetyl]-2,6-di(propan-2-yl)phenyl] sulfamate Chemical compound COC1=CC=CC=C1CC(=O)C1=CC=C(C(C)C)C(OS(N)(=O)=O)=C1C(C)C VWMCJIVWYXESEB-UHFFFAOYSA-N 0.000 claims description 2
- ODLHXSJZGOAYGM-UHFFFAOYSA-N [3-[2-[2,6-di(propan-2-yl)phenyl]acetyl]-2,4,6-tri(propan-2-yl)phenyl] sulfamate Chemical compound CC(C)C1=CC=CC(C(C)C)=C1CC(=O)C1=C(C(C)C)C=C(C(C)C)C(OS(N)(=O)=O)=C1C(C)C ODLHXSJZGOAYGM-UHFFFAOYSA-N 0.000 claims description 2
- XBVKHCGXRZSBCL-UHFFFAOYSA-N [3-[2-[2,6-di(propan-2-yl)phenyl]acetyl]-2,6-di(propan-2-yl)phenyl] sulfamate Chemical compound CC(C)C1=CC=CC(C(C)C)=C1CC(=O)C1=CC=C(C(C)C)C(OS(N)(=O)=O)=C1C(C)C XBVKHCGXRZSBCL-UHFFFAOYSA-N 0.000 claims description 2
- DXHYZVZSMDLNBQ-UHFFFAOYSA-N [3-decanoyl-2,6-di(propan-2-yl)phenyl] sulfamate Chemical compound CCCCCCCCCC(=O)C1=CC=C(C(C)C)C(OS(N)(=O)=O)=C1C(C)C DXHYZVZSMDLNBQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 2
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 2
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- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
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- 235000014380 magnesium carbonate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 210000004175 meibomian gland Anatomy 0.000 description 1
- 230000003340 mental effect Effects 0.000 description 1
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- 239000004005 microsphere Substances 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
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- 235000013536 miso Nutrition 0.000 description 1
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- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 239000002077 nanosphere Substances 0.000 description 1
- 235000021096 natural sweeteners Nutrition 0.000 description 1
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 1
- KSCKTBJJRVPGKM-UHFFFAOYSA-N octan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCCCCCC[O-].CCCCCCCC[O-].CCCCCCCC[O-].CCCCCCCC[O-] KSCKTBJJRVPGKM-UHFFFAOYSA-N 0.000 description 1
- 239000003605 opacifier Substances 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 229940100688 oral solution Drugs 0.000 description 1
- 239000007935 oral tablet Substances 0.000 description 1
- 229940096978 oral tablet Drugs 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical class C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
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- 229940049954 penicillin Drugs 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229940124606 potential therapeutic agent Drugs 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- ALDITMKAAPLVJK-UHFFFAOYSA-N prop-1-ene;hydrate Chemical group O.CC=C ALDITMKAAPLVJK-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000004508 retinoic acid derivatives Chemical class 0.000 description 1
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- 239000002453 shampoo Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000007910 systemic administration Methods 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 229960002180 tetracycline Drugs 0.000 description 1
- 229930101283 tetracycline Natural products 0.000 description 1
- 235000019364 tetracycline Nutrition 0.000 description 1
- 150000003522 tetracyclines Chemical class 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 238000011285 therapeutic regimen Methods 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 229940100611 topical cream Drugs 0.000 description 1
- 239000006208 topical dosage form Substances 0.000 description 1
- 229940042129 topical gel Drugs 0.000 description 1
- 229940100617 topical lotion Drugs 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
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- 239000000196 tragacanth Substances 0.000 description 1
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- FLTJDUOFAQWHDF-UHFFFAOYSA-N trimethyl pentane Natural products CCCCC(C)(C)C FLTJDUOFAQWHDF-UHFFFAOYSA-N 0.000 description 1
- 229960005486 vaccine Drugs 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/64—Sulfonylureas, e.g. glibenclamide, tolbutamide, chlorpropamide
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/18—Sulfonamides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/255—Esters, e.g. nitroglycerine, selenocyanates of sulfoxy acids or sulfur analogues thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/27—Esters, e.g. nitroglycerine, selenocyanates of carbamic or thiocarbamic acids, meprobamate, carbachol, neostigmine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/325—Carbamic acids; Thiocarbamic acids; Anhydrides or salts thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/08—Antiseborrheics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/10—Anti-acne agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/16—Emollients or protectives, e.g. against radiation
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/38—Drugs for disorders of the endocrine system of the suprarenal hormones
Landscapes
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dermatology (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Diabetes (AREA)
- Toxicology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US30933601P | 2001-08-01 | 2001-08-01 | |
| US60/309336 | 2001-08-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JP2003104878A true JP2003104878A (ja) | 2003-04-09 |
Family
ID=23197778
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002222616A Pending JP2003104878A (ja) | 2001-08-01 | 2002-07-31 | 皮脂生産を阻害するためのワックス・エステルとコレステリル・エステル合成の２重阻害剤 |
Country Status (11)
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007508291A (ja) * | 2003-10-09 | 2007-04-05 | ワーナー−ランバート カンパニー リミテッド ライアビリティー カンパニー | 皮脂産生を減少させるためのマロンアミド誘導体を含んでなる医薬組成物 |
| JP2021534148A (ja) * | 2018-08-15 | 2021-12-09 | インフレイゾーム リミテッド | 新規スルフォンアミドウレア化合物 |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7144911B2 (en) | 2002-12-31 | 2006-12-05 | Deciphera Pharmaceuticals Llc | Anti-inflammatory medicaments |
| US7202257B2 (en) | 2003-12-24 | 2007-04-10 | Deciphera Pharmaceuticals, Llc | Anti-inflammatory medicaments |
| US7279576B2 (en) | 2002-12-31 | 2007-10-09 | Deciphera Pharmaceuticals, Llc | Anti-cancer medicaments |
| CA2592118C (en) | 2004-12-23 | 2015-11-17 | Deciphera Pharmaceuticals, Llc | Urea derivatives as enzyme modulators |
| US8188113B2 (en) | 2006-09-14 | 2012-05-29 | Deciphera Pharmaceuticals, Inc. | Dihydropyridopyrimidinyl, dihydronaphthyidinyl and related compounds useful as kinase inhibitors for the treatment of proliferative diseases |
| US7790756B2 (en) | 2006-10-11 | 2010-09-07 | Deciphera Pharmaceuticals, Llc | Kinase inhibitors useful for the treatment of myleoproliferative diseases and other proliferative diseases |
| JP2010524974A (ja) | 2007-04-20 | 2010-07-22 | デシファラ ファーマスーティカルズ， エルエルシー | 骨髄増殖性疾患および他の増殖性疾患の治療に有用なキナーゼ阻害剤 |
| CA2742007C (en) | 2008-10-29 | 2014-07-08 | Deciphera Pharmaceuticals, Llc | Cyclopropane amides and analogs exhibiting anti-cancer and anti-proliferative activities |
| US8461179B1 (en) | 2012-06-07 | 2013-06-11 | Deciphera Pharmaceuticals, Llc | Dihydronaphthyridines and related compounds useful as kinase inhibitors for the treatment of proliferative diseases |
| KR20180133244A (ko) | 2016-02-16 | 2018-12-13 | 더 유니버서티 어브 퀸슬랜드 | 설포닐유레아 및 관련 화합물 및 이의 용도 |
| GB201721185D0 (en) | 2017-12-18 | 2018-01-31 | Nodthera Ltd | Sulphonyl urea derivatives |
| KR102708177B1 (ko) | 2018-01-31 | 2024-09-23 | 데시페라 파마슈티칼스, 엘엘씨. | 위장관 기질 종양의 치료를 위한 병용 요법 |
| EP3746060A1 (en) | 2018-01-31 | 2020-12-09 | Deciphera Pharmaceuticals, LLC | Combination therapy for the treatment of mastocytosis |
| LT3983387T (lt) | 2019-06-12 | 2024-07-25 | NodThera Limited | Sulfonilkarbamido dariniai ir jų naudojimas |
| JP2022544234A (ja) | 2019-08-12 | 2022-10-17 | デシフェラ・ファーマシューティカルズ，エルエルシー | 胃腸間質腫瘍を治療するためのリプレチニブ |
| WO2021030405A1 (en) | 2019-08-12 | 2021-02-18 | Deciphera Pharmaceuticals, Llc | Ripretinib for treating gastrointestinal stromal tumors |
| FI4084779T3 (fi) | 2019-12-30 | 2024-12-16 | Deciphera Pharmaceuticals Llc | 1-(4-bromi-5-(1-etyyli-7-(metyyliamino)-2-okso-1,2-dihydro-1,6-naftyridin-3-yyli)-2-fluorifenyyli)-3-fenyyliurean koostumuksia |
| LT4084778T (lt) | 2019-12-30 | 2024-01-25 | Deciphera Pharmaceuticals, Llc | Amorfinės kinazės inhibitoriaus vaistinės formos ir jų panaudojimo būdai |
| US11779572B1 (en) | 2022-09-02 | 2023-10-10 | Deciphera Pharmaceuticals, Llc | Methods of treating gastrointestinal stromal tumors |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4716175A (en) * | 1987-02-24 | 1987-12-29 | Warner-Lambert Company | Saturated fatty acid amides as inhibitors of acyl-CoA:cholesterol acyltransferase |
| US5245068A (en) * | 1990-10-30 | 1993-09-14 | Warner-Lambert Company | Oxysulfonyl carbamates |
| US5254715A (en) * | 1990-11-07 | 1993-10-19 | Warner-Lambert Company | Aminosulfonyl carbamates |
| US5214206A (en) * | 1990-11-07 | 1993-05-25 | Warner-Lambert Company | Aminosulfonyl urea acat inhibitors |
| US5198466A (en) * | 1990-11-09 | 1993-03-30 | Warner-Lambert Company | Oxysulfonyl urea acat inhibitors |
| ZA938019B (en) * | 1992-11-13 | 1995-04-28 | Upjohn Co | Pyran-2-ones and 5,6-dihydropyran-2-ones useful for treating HIV and other retroviruses |
| IL109431A (en) * | 1993-05-14 | 2001-01-11 | Warner Lambert Co | Pharmaceutical compositions containing n-acyl sulfamic acid esters (or thioesters), n-acyl sulfonamides, and n-sulfonyl carbamic acid esters (or thioesters), for regulating plasma cholesterol concentration, and certain such novel compounds |
| US5491172A (en) * | 1993-05-14 | 1996-02-13 | Warner-Lambert Company | N-acyl sulfamic acid esters (or thioesters), N-acyl sulfonamides, and N-sulfonyl carbamic acid esters (or thioesters) as hypercholesterolemic agents |
| US6133326A (en) * | 1994-08-31 | 2000-10-17 | Pfizer Inc | Compositions and methods for decreasing sebum production |
| EA004255B1 (ru) * | 2000-02-02 | 2004-02-26 | Уорнер-Ламберт Компани | Применение 2,6-диизопропилфенилового эфира [(2,4,6-триизопропилфенил)ацетил]сульфаминовой кислоты в качестве ингибитора секреции сальных желез, в частности, для лечения акне и композиции и способы на основе данного соединения |
| US6514489B1 (en) * | 2000-06-30 | 2003-02-04 | Medicis Pharmaceutical Corp. | Sulfur containing dermatological compositions and methods for reducing malodors in dermatological compositions |
| US6852738B2 (en) * | 2001-01-30 | 2005-02-08 | Merck & Co., Inc. | Acyl sulfamides for treatment of obesity, diabetes and lipid disorders |
-
2002
- 2002-07-23 EP EP02255156A patent/EP1281399A3/en not_active Withdrawn
- 2002-07-25 CA CA002395006A patent/CA2395006A1/en not_active Abandoned
- 2002-07-25 IL IL15091802A patent/IL150918A0/xx unknown
- 2002-07-29 ZA ZA200206032A patent/ZA200206032B/xx unknown
- 2002-07-31 NZ NZ520487A patent/NZ520487A/en unknown
- 2002-07-31 JP JP2002222616A patent/JP2003104878A/ja active Pending
- 2002-07-31 US US10/209,236 patent/US20030134898A1/en not_active Abandoned
- 2002-07-31 HU HU0202548A patent/HUP0202548A2/hu unknown
- 2002-07-31 CN CN02127403A patent/CN1404829A/zh active Pending
- 2002-07-31 KR KR1020020045396A patent/KR20030013289A/ko not_active Ceased
- 2002-07-31 PL PL02355281A patent/PL355281A1/xx not_active Application Discontinuation
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007508291A (ja) * | 2003-10-09 | 2007-04-05 | ワーナー−ランバート カンパニー リミテッド ライアビリティー カンパニー | 皮脂産生を減少させるためのマロンアミド誘導体を含んでなる医薬組成物 |
| US8409595B2 (en) | 2003-10-09 | 2013-04-02 | Medicis Pharmaceutical Corporation | Method for decreasing sebum production |
| JP2021534148A (ja) * | 2018-08-15 | 2021-12-09 | インフレイゾーム リミテッド | 新規スルフォンアミドウレア化合物 |
Also Published As
| Publication number | Publication date |
|---|---|
| IL150918A0 (en) | 2003-02-12 |
| CA2395006A1 (en) | 2003-02-01 |
| HU0202548D0 (enrdf_load_html_response) | 2002-10-28 |
| EP1281399A2 (en) | 2003-02-05 |
| KR20030013289A (ko) | 2003-02-14 |
| EP1281399A3 (en) | 2004-02-11 |
| HUP0202548A2 (hu) | 2003-02-28 |
| ZA200206032B (en) | 2004-02-10 |
| US20030134898A1 (en) | 2003-07-17 |
| PL355281A1 (en) | 2003-02-10 |
| CN1404829A (zh) | 2003-03-26 |
| NZ520487A (en) | 2004-03-26 |
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